From Cool to Tool: Tracking Barack Obama's Descent Into Toolbaggery

as a toddler

Short-sleeve woven is fine. White shoes acceptable if you're under four years old and look preternaturally idealistic. But that hat? Foreshadows poor headwear choices to come.

as an early teen

Evoking a certain King of Pop before "Thriller" and plastic surgery, Obama looks happy and should be, with fly afro and "I Ski" sunglasses years before they hit peak popularity.

in high school

Most Americans are justifiably embarrassed by their high school-era style. Barack Obama, on the other hand, is peaking in high school, exuding a confident, casual cool most men never achieve.

(very) early college years

Obama smoking a cigarette with style and panache on par with FDR (inset).

at columbia (undergrad)

Forget the Great Depression. The Great Decline can be traced to enrollment into Columbia University. Out is the afro and devil-may-care carriage. In is seriousness and an un-ironic leather Members Only jacket.

at harvard (law school)

At Harvard Law School Obama abandoned any sense of style, apparently in favor of utility. That anorak has enough strings and buckles and zippers for at least three coats. This is Cambridge, not Everest! There are barely even any stairs to climb. Digital watch completes policy wonk look. "Washington, D.C., here I come."

stumping for votes

The campaign trail did more damage than Columbia and Harvard combined. Obama stumping for votes in Austin was nearly a Dukakis Event, an accessory that did not work on any level except public ridicule.

the first pitch

We'll cut him some slack for the untucked jersey, but soccer dad jeans and space-age running shoes are definitely no way to dress for a first pitch. Or ever.

on the golf course

Either this is the president-elect or Phil from Accounts Payable. Cargo shorts, over long-sleeve polo, and a fucking Blackberry on his waist on a golf course puts Obama solidly in toolbag category.

the 44th president of the united states

We can all agree with Barack Obama on one thing: CHANGE!

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